


The Hole

by Kat210



Category: Supernatural
Genre: Alternate Universe - College/University, Anal Sex, Bottom Dean, Cock Slut Dean Winchester, Cum Eating, Double Penetration, Gangbang, M/M, Plot What Plot/Porn Without Plot, Submissive Dean, face fucking
Language: English
Status: Completed
Published: 2020-01-08
Updated: 2020-01-08
Packaged: 2021-02-27 12:14:46
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 3,856
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22166974
Author URL: https://archiveofourown.org/users/Kat210/pseuds/Kat210
Summary: Dean's joining a fraternity, partially because he really likes their President, one Castiel Novak who likes to be referred to as God. Of course their hazing is a bit different. Two pledges go up against each other, whoever can get the other's toga off (a loosely tied sheet), and plug out and get their dick in first wins. The loser ends up being the frat's "hole."
Relationships: Castiel/Dean Winchester, Dean Winchester/Others
Comments: 5
Kudos: 301





	1. Chapter 1

Dean Winchester let out a deep breath as he stared at the closed door across the hall from him. The 18 year old glanced to the young men standing on either side of him. All nine of them were dressed exactly the same and all had the same expression of nervousness and anticipation on their faces. The college boy assumed they also had the same preparations he did.   
The Vice President of the fraternity cleared his throat as he stopped with his back to the closed door. He nodded at one of the other men who had entered the hall with him before opening the door. Dean was led into the room, by his soon to be fraternity brothers, the others following him. He tugged slightly on the sheet that was wrapped as a toga around his body, the fabric loosely tied, all the more easy to get off. He came to a stop across from the fraternity's president. It was the view here that really had Dean's breathing quicken.   
The dark haired man lolled on a chair (which the brothers referred to as his throne), in a white dress shirt, and black dress pants, a fire blazing in the fireplace behind him. The shirt was unbuttoned. Dean bit down a groan at the sight of two well formed nipples. The President, better known as God, glanced over at the pledges lazily before sitting up straight. Blue eyes moved over each of the nine young men standing across from him. Dean could feel his heart pounding in his chest at the feel of those eyes on him, arousal churning through his body. 

Castiel was the reason Dean wanted to join this frat. Even after hearing the rumors of what they made the pledges do before joining. What one pledge would then be required to do until he decided to have another take his place, or graduated college. The rumors that had turned out to be true. Or perhaps they were just another incentive for Dean to join. The freshman's cock twitched under his sheet. Castiel's eyes glanced downwards, before breaking out into a smile.   
"Okay boys, you know what our God here wants," said the vice president, Gabe. He grinned at them.   
Dean swallowed hard when he saw the obvious tent forming in Castiel's pants. His eyes flickered up only to have said man wink at him.   
"Okay Deano, you're up," Gabe gestured to him. The green eyed man moved into the center of the room. Benny was the next to join him. They stood across from each other waiting. Dean took the moment to examine Benny. He was about his own height, but was much broader throughout his chest. He'd be a tough one to beat.   
"Go ahead," Cas said, his gravelly voice deepening Dean's arousal. Benny moved across to snatch Dean who ducked out of the way before spinning to face the bigger man. Benny grinned and winked before coming at Dean again. This time he got his hands on the toga Dean was wearing and tugged at it. There was a faint ripping noise and the top part tore so it was now hanging down, leaving the young man's chest exposed.   
There was a sharp whistle, "looking sexy Deano!" 

The man ignored Gabriel, making his own attempt at grabbing at Benny's toga, but missed. Hands grabbed at Dean and flipped him onto the floor face down. Dean went to move away, but ended up only aiding Benny in completely ripping his toga off. He turned and managed to get up, leaving Benny with the sheet.   
"Nice dick," came a shout from one of the other brothers as the freshman stood there naked. Dean ignored it. They were only trying to distract him. He also refused to look at Cas, knowing he'd only sidetrack him. 

"Oh Benny if only you could see him from this end," came another shout and laughter from behind. Dean watched as the other man started to slowly approach him. No, he wasn't going to let Benny win this. He was going to beat everyone and impress Castiel. It was then that Dean's green eyes caught the President of the frat, who enjoyed being referred to as a God watching him. Or more accurately staring at what was between his legs. A brief second later he realized his mistake when he found himself on the ground, Benny pulling the plug out of his hole. And then he felt his cock spear him from behind.  
The man let out a moan as he was fucked into the floor in front of his soon to be frat brothers. He kept his face down as the brothers shouted out lewd comments. Benny came into him and pulled out.   
Dean lay on the floor as Benny stood up and straightened out his toga. Castiel nodded at Benny as he joined the brothers on their side of the room.   
"Alright Deano, time to try again," Gabe forced him up on shaky legs. "Remember now that you've lost once, your condition remains the same. No more toga or plug." Gabe grinned. "Let's see if you can beat the next guy and fuck him first."   
As Nick came towards Dean, he was acutely aware of the cum slipping down between his ass cheeks. And the fact that his back was to Castiel. And he was slightly aroused. He glanced at Nick to see that he was also aroused. Dean managed to get a hand on the toga, which ripped slightly, but still remained on the other man. Nick grabbed at Dean and managed to force him on the floor, but Dean wiggled out and got back up. They grabbed onto each other and Dean managed to get the toga completely off, leaving them both nude. The brothers were going crazy now, shouting out crude comments at both of them.   
He was going to win this, he just knew it. Then Nick slid a foot under Dean's knocking him to the ground again. Dean fought as Nick got on top of him, but was flipped over. The second dick of the night found his hole and Nick began fucking him, harder than even Benny.   
Dean let out little gasps and moans as his prick rubbed against the carpeting on the floor. He was approaching orgasm now. Then he felt the feeling of cum in him again and Nick pulled out. The man's arousal faded a bit without the stimulus.   
Yet again, Gabe pulled him up. Dean's legs were trembling now as the next soon to be frat brother approached.  
Victor smiled at him. Dean wanted to groan. Victor spent a lot of time at the gym. He was also really attractive. It didn't take long before he had pushed Dean against the wall and was pounding into him from behind, his balls slapping Dean's ass with every thrust. Once again he approached his orgasm and once again, his partner finished and pulled out, leaving Dean frustrated.   
Gabe pulled Dean back over to the center of the room. The brothers were talking and passing money back and forth. He saw several others eying him with obvious interest, as he stood there naked, cum dripping from his asshole. A small part of him still wanted to win so he wouldn't be the frat's hole, but a growing part was really starting to enjoy all these men fucking him.   
His penis was curved up, dripping precum at this point, Dean didn't think he'd ever been so hard before in his life. He was so tempted to touch himself, but he knew that that wouldn't be allowed.   
The fourth pledge stepped up. He grinned at Dean, clearly confident in his ability to beat him. Dean managed to get his toga off and his plug out before Gordon turned the tables and flipped him onto his lap, dick driving up into Dean's used hole, and began moving his hips. The 18 year old couldn't help it, moans and pleas began falling from his lips.   
"Harder," he begged as his head fell back, as he moved his own body in time with the other man. His body was on fire, pleasure overtaking him. There was movement and he was on his hands and knees as the other pledge plunged deeper into him with the change in position.   
Dean was so close, he could feel it coming. Then he felt the familiar feeling of cum in his ass and Gordon grunted as he pulled out.   
The freshman was wobbling on his legs as pledge number five stepped up. His ass was really beginning to hurt even as his arousal became harder to push down. His cock bounced with every step he took and the frat brothers were no longer being quiet about their thoughts on him and his body. How he would be the most attractive hole/slut/whore they'd had over the past few years. A good number of them had tents in their pants, as they stared lustfully at Dean.   
"His moans-", "Do you see his hole? And the amount of cum dripping from it?", "His lips would look so good wrapped around my dick-" "I just want to bend him over and spank him-"  
Dean chanced a look at Castiel as the sixth pledge was speeding up his thrusts. His vision went dark as he came from the sight of the dark haired man who had lost his shirt completely and had his pants unzipped, cock poking out.   
He felt himself being forced up, as Gabe pushed him back to his spot. Dean's vision cleared as he stared at pledge number seven and the very big tent that was showing through his toga. His legs were very shaky now and he slowly became aware his cum had gotten onto his chest, a few drops making it as far as his chin. He stood there trembling, not even fighting back as the other man came at him. He went down onto his knees willingly and stuck his ass out so the other could take him. Right before the other man came, he struck that spot in Dean that had him groaning as his cock began to spring back to life.   
"Quick turnaround. He must love getting that ass pounded," one of the brothers said. Dean hobbled to his feet as the last pledge came forward. He moved toward the pledge falling onto his knees, pushing the toga aside and took the cock into his mouth, giving his ass a much needed break. A groan spilled out of the mouth of the other man as Dean sucked and licked, allowing him to fuck his face.   
"Look at how he takes it. He was born for this, he's deep throating him. Done this before hole?" A brother called out.   
The last pledge pulled out, cum spilling onto Dean's face.   
"Well we have our new hole," Castiel said, standing up. The brothers cheered as Dean knelt, cum dripping off of him and out of him.   
"Take him to my room. You all will have your turn with him tomorrow!" he called out.


	2. Chapter 2

Dean entered Castiel's room. "Stand here and wait until your new God tells you otherwise," the vice president ordered. Gabriel then turned and left, leaving the door open behind the new fraternity brother.  
Green eyes stared at the king sized bed as well as the fire that burned in the fire place. "Go lay down," the fraternity's president's body was pressed up behind Dean's, lips grazing his ear as he whispered softly. The freshman shivered at the feel of clothing brushing his bare skin. Reluctantly he moved and lay down on the soft sheets, hissing when the ache in his ass brought itself to his attention. He was so incredibly sore and tired. But he was far more satiated than he'd ever remembered being before. Upon becoming a pledge he'd thought he'd win this competition and impress Castiel with his fucking skills. He'd never imagined he'd lose and become the fraternity's hole. To be used at the brothers' whim. Yet, he'd enjoyed it far more than he'd thought. The idea of being bent over and fucked so mercilessly had his cock twitching. So many men having their hands on him, and their cocks in him, he'd never realized how much he craved that. Sure, he'd been with men before, sucked their dicks and all of that. In fact his oral skills were awesome if he did say so himself. He'd very quickly learned how to deep throat back in high school. But this, being gang banged and used, it was kink he never realized he had.  
Dean jumped when he felt a cool liquid poured on to his asshole. The bed sank down as another climbed onto it.  
"Shhhh, just something to help with the soreness," Castiel whispered, rubbing the lotion into him. Dean let out a low moan.  
Cas pulled his hand away and the freshman felt a plug, slightly bigger than the first slide into him.  
"Sleep," Castiel whispered, as he brushed his hand down Dean's back. "We'll play later." The blond drifted to sleep, lulled by the warmth of the naked body curled around his.  
Dean woke up gasping. The fingers in him moved again, pleasure shooting through him. "Playtime," Cas said, pulling his fingers out and rolling the freshman onto his stomach before mounting him.  
Dean's mouth fell open as he was speared from behind. His cock was fully hard and dripping as the older man drove into him. The bed shook from the force behind the thrusts.  
Fingers clenched the sheets as his lust rose.  
"Harder," Dean grunted. "Fuck me harder," he begged. Castiel sped up, the headboard now banging against the wall. For a brief moment Dean's mind wandered to the other brothers. Were they listening? Could they hear their President, their God fucking him? Were they now touching themselves, waiting for the moment they could get their hands on him? These thoughts drove Dean up the edge of orgasm. Warmth spurted into his ass as Castiel came hard. Dean was panting as the other pulled out, shoving the plug back in, keeping his cum inside. The freshman stared down at himself seeing the cock ring that had kept him from coming, for the first time.  
A sharp pain brought Dean back to reality. He went to flip over to look, but Castiel shoved him back down on the bed. The manhandling made him let out a groan. Another slap to his ass.  
"Your ass looks so pretty all pink like that," Castiel told him, as he continued spanking his lover. Slap. Slap. Dean shoved his dick down against the soft sheets, trying to ease the pressure. Slap. Slap. One landed on the plug, driving it further into him. He was moaning loud now.  
"They can hear us you know," Castiel informed him. Slap. "They're probably imagining screwing you." Slap. Slap. "Who can blame them with the way you moan? Like a whore. You love being bent over and fucked. You love being used. And spanked. You're the perfect little hole. And I bet you're going to keep this position until you graduate. And then you'll be sad at leaving it." He rubbed Dean's ass, the soreness making him even harder. He ached to cum. Cas forced Dean around and his head up. The freshman choked slightly as the man shoved his cock into his mouth and began brutally face fucking him. After a couple of thrusts, Dean adjusted, drool dripping down his chin. Castiel's balls hit his face as he moved in and out. Dean's hands had fallen on the other's hips as he clenched onto him.  
Castiel was breathing hard as he moved. "So good at this, you little slut," he gasped out. He yanked out suddenly and then Dean's face was covered in cum. He stared up at the blue eyed man, as it dripped off of him and onto the bed.  
"Lick it up," Castiel commanded gesturing at the liquid on the bed. Dean obeyed, licking the sheets clean before using his hands to wipe his face. He licked his hands clean as well.  
"The perfect little hole," Cas said as he laid back on the bed, pulling Dean down with him. Dean stared at his cock still sticking up straight and dripping, the cock ring tight on him.  
"Go get me a water bottle from downstairs," Castiel commanded suddenly. The freshman got up."Don't put anything on," the President said. Dean opened the door and walked down the hall, his prick bobbing up and down with each step.  
"There's the hole," one of the brothers called out. The others came to their doors and watched the hole move through the hallway.  
"Look at how hard he is. He's enjoying it." Another called out.  
"Whoa, look at those handprints on his ass," said another. "You're a bad boy aren't you?" a third called out.  
"Only a few more hours and you'll be ours," Dean glanced at the brother who said this. He was standing naked in his doorway, his own cock glistening as he stared lustfully at the newest member of the fraternity. The catcalls died down when Dean made it to the kitchen. The brothers were still waiting as he made his way back though.  
"We could hear you beg, 'fuck me harder'" the brother laughed as he called out. "A few hours hole, and you're mine."  
"Gonna use you up good," another called, a tent in his sweats obvious. "Bet we can get more than one cock in that greedy hole of yours."  
A groan slipped out of Dean at the thought. Laughter followed as he shut Castiel's door behind him.  
Hands were on him, the water bottle slipping to the floor as Castiel shoved him on the bed. Dean cried out as the other man shoved into him and began pounding away again. The blankets rubbed at the hole's sensitive nipples. He paused part way through, reaching down to remove the cock ring and then resumed screwing Dean, hips moving faster and faster. Dean came hard, screaming as he came for what felt like forever. It took him awhile to realize his President was lying on top of him, spent from his own orgasm. Dean could feel the cum trickling down the back of his legs.  
Castiel continued to fuck Dean several more times throughout the night, the freshman coming hard each time. His ass was beyond sore by the time the sun began to rise. The President gave him water and food, before rubbing some more of the lotion into his ass.  
"Sleep. Once the brothers get their hands on you, it'll be awhile before you get any more rest."  
Dean slept.


	3. Chapter 3

The sun was low in the sky by the time Dean woke. Castiel was watching him with his intense blue eyes, now clothed. He smiled gently at the still sleep confused man.   
"It's time, Dean," he said softly. Said man stared, brain not understanding what he was being told. Time for what?   
"Just like all of you pledges were tested, everyone here has been tested. Once a month, every month. So you don't have to worry about that," Castiel informed him.   
That's when it clicked. Oh right. The other brothers. Dean felt his cock began to stir.   
The President led him down the stairs, the top floor oddly quiet. His dick bounced with each step down to the bottom floor. Down to where a bunch of young men were waiting to pound into Dean. The freshman shivered at the thought. Castiel paused as they reached the bottom floor. He bent down and put the cock ring onto Dean. He straightened up and then grinned at the other man. 

"They would like to be able to enjoy you for a little while," he whispered as he stepped into the freshman's space. He reached out and flicked the hardened nipples before turning Dean around and pressing him up against the wall. Dean moaned when Cas spanked his ass a couple of times.   
"So they don't forget who you belong to," Cas growled, his voice low. He then opened the door and pushed Dean into the room. The brothers turned and stared at the naked man.   
"There's our hole," one of them said. All of the brothers were stripped bare, Dean swallowed when he saw all of those cocks jutting out, hard just for him and slathered in lube.   
They began circling around him, pulling him further into the room. "Ah it seems our God marked you," one of them said, touching his ass. "You can still see his handprint," he laughed. 

Balthazar reached out and pulled Dean so his back was pressed against his front. The freshman could feel the dick pressed against him. He groaned when a hand reached down to grab his erection. The junior licked his neck.   
"Delicious," he said into Dean's ear. Without warning he shoved into the younger man and began furiously pounding him. Hands gripped onto his hips as his legs went weak. A senior, Michael came up to Dean from his front. He rutted against him, their dicks brushing. 

"Ooooh," the man cried out. He was so hard. Balthazar came into him and pulled out. Michael paused in his own movements. Dean felt another cock press into him. His mouth widened as after a moment of movement behind him, a second one stretched his hole. He was so fucking full. The three men began moving, breathing heavily as Dean's body was jostled between them. Michael came hard, cum shooting all over Dean. The two behind him began fucking him faster and faster. After they finished they pulled away. Dean's legs buckled and he began to fall. Arms went around him, catching him. 

"Told you you're mine," the brother from earlier kissed him on his neck before bringing him down into his lap.   
"Fuck," Dean said as he was filled again. He began riding the other man hard, starting a mantra of "fucks" with each bounce. Cum shot up into him and he was moved gingerly off, his body being laid down onto the couch. Hands moved his body and once again, he had two penises shoved into his sore hole. Dean moaned. He was so full. He'd never felt so full before. His cock was aching. He wanted to cum, needed to cum. Tears were streaming down his face now. The two brothers finished and pulled out. More brothers came. They shoved two cocks into his mouth. Dean gagged, but managed to push his reflex down as he was face fucked. 

Hours passed as he was passed around. Cum covered his body and his stomach and ass were filled over and over. Finally the cock ring was pulled off as he was being screwed. He came so hard he blacked out. When he opened his eyes he found he was laying on the floor, still covered with not one of the brothers in sight. He sat up with a groan. Then he looked toward the door. Castiel was watching him his dick hard.   
•


End file.
